Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- 19-norandrostenedione
- DrugBank Accession Number
- DB01434
- Background
19-Norandrostenedione refers to two steroid isomers that were once marketed as dietary supplements and mainly used by body builders. After 2005, 19-Norandrostenedione was regulated in the United States as a schedule III controlled substance, as well as banned from use in competitive sports by the World Anti-Doping Agency.
In the body 19-norandrostenedione is rapidly metabolized into nandrolone, also known as nortestosterone.
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for 19-norandrostenedione (DB01434)
- Weight
- Average: 272.382
Monoisotopic: 272.177630012 - Chemical Formula
- C18H24O2
- Synonyms
- delta,4-Estrene-3,17-dione
- delta4-Estrene-3,17-dione
- External IDs
- NSC-12164
Pharmacology
- Indication
The claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.
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Not Available
- Mechanism of action
19-Norandrostenedione may be metabolized to 19-nortestosterone in both men and women. 19-Norandrostenedione, also known as nandrolone, is the basic substance of some very popular injectable anabolic steroids, however 19-norandrostenedione is not metabolized to testosterone. Whether or not increases in 19-nortestosterone levels would be sustained long enough by taking 19-norandrostenedione to show an increase in nitrogen retention and muscle strength and mass is unknown.
19-Norandrostenedione has also been shown to bind to androgen receptors with high selectivity. Transactivation of androgen receptor dependent reporter gene expression was 10 times lower than that produced by dihydrotestosterone. [1]
- Absorption
Absorption appears variable, but some absorption does occur.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Specific metabolites of 19-nor-5-androstene-3, 17-dione are 19-nordehydroandrosterone and 19-nordehydroepiandrosterone.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareBeclomethasone dipropionate The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Beclomethasone dipropionate. Betamethasone The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Betamethasone. Betamethasone phosphate The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Betamethasone phosphate. Budesonide The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Budesonide. Ciclesonide The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Ciclesonide. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrogens and derivatives
- Alternative Parents
- 3-oxo delta-4-steroids / 17-oxosteroids / Delta-4-steroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Cyclohexenone / Delta-4-steroid / Estrogen-skeleton / Hydrocarbon derivative
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3-oxo steroid (CHEBI:34187)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- U90987PVU5
- CAS number
- 734-32-7
- InChI Key
- JRIZOGLBRPZBLQ-QXUSFIETSA-N
- InChI
- InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1
- IUPAC Name
- (3aS,3bR,9aR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione
- SMILES
- [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
References
- General References
- Diel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Schleipen B, Thevis M, Vollmer G, Zierau O: The prohormone 19-norandrostenedione displays selective androgen receptor modulator (SARM) like properties after subcutaneous administration. Toxicol Lett. 2008 Apr 1;177(3):198-204. doi: 10.1016/j.toxlet.2008.01.014. Epub 2008 Feb 2. [Article]
- External Links
- KEGG Compound
- C14500
- PubChem Compound
- 92834
- PubChem Substance
- 46505377
- ChemSpider
- 83803
- ChEBI
- 34187
- ZINC
- ZINC000004428372
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- 19-Norandrostenedione
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0454 mg/mL ALOGPS logP 2.53 ALOGPS logP 3.63 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 18.25 Chemaxon pKa (Strongest Basic) -4.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 34.14 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 79.13 m3·mol-1 Chemaxon Polarizability 31.56 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9723 Caco-2 permeable + 0.7785 P-glycoprotein substrate Substrate 0.5551 P-glycoprotein inhibitor I Inhibitor 0.8097 P-glycoprotein inhibitor II Non-inhibitor 0.6972 Renal organic cation transporter Non-inhibitor 0.638 CYP450 2C9 substrate Non-substrate 0.827 CYP450 2D6 substrate Non-substrate 0.9064 CYP450 3A4 substrate Substrate 0.6816 CYP450 1A2 substrate Non-inhibitor 0.8259 CYP450 2C9 inhibitor Non-inhibitor 0.9269 CYP450 2D6 inhibitor Non-inhibitor 0.94 CYP450 2C19 inhibitor Non-inhibitor 0.7094 CYP450 3A4 inhibitor Non-inhibitor 0.8652 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7931 Ames test Non AMES toxic 0.9189 Carcinogenicity Non-carcinogens 0.9403 Biodegradation Not ready biodegradable 0.9401 Rat acute toxicity 1.6104 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7011 hERG inhibition (predictor II) Non-inhibitor 0.7574
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 167.90257 predictedDeepCCS 1.0 (2019) [M+H]+ 170.19145 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.62697 predictedDeepCCS 1.0 (2019)
Drug created at July 24, 2007 20:36 / Updated at June 12, 2020 16:51